Previous Previous ImageNext Next Image
Slideshow Divider

Our mobile site is optimized for smaller screens.

TRY IT NO THANKS

Chester VT Real Estate

Search the latest real estate in Chester, VT with Maple Sweet Real Estate. Find the right property for you from a variety of listings. To save your favorites, register with us and you can get email notifications when similar properties are posted. Already have an account with us? Log in here.

For more information, any questions you may have & to schedule a show, please feel free to give us a call or contact us online.

339 Richardson Road Chester VT 05143

Chester, VT339 Richardson Road

Price$1,499,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4842176

  • Residential Single Family
  • Construction Existing
  • Bedrooms 9
  • Bathroom 5
  • Square Feet 4,326

This home with over 207 accessible acres in both Chester and Andover is perfect for a large family or group. 9 bedrooms including master suite on first floor, 5 full baths, large public spaces, and an oversized 3 bay heated garage with full finished storage room overhead. Privately set between Chester, Londonderry and Weston with soufthern and western views. Top quality, recent construction and all amenities: granite counters, double ovens, central AC, radiant and baseboard heating, large stone fireplace, full house automatic generator, shining wood floors, and comfortable dining seating for 15-20. Sled, ski or snowmobile through the front yard, meadows or wooded trails. Small pond in view from front porch. The land is enrolled in VT Current Use and VT Land Trust for tax reduction and land conservation. Most house furnishings are included - list available.

Listed by Judy Dickison of Barrett & Valley Associates, Inc.

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 2.98% last updated on 2021-04-29

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

134 Gold River Extension Chester VT 05143

Chester, VT134 Gold River Extension

Price$1,490,000The price has recently decreased

MLS Number 4837125

  • Commercial
  • Acreage 13.42

Rare opportunity with commercial/industrial zoning. 13+ acres of fully permitted subdividable lots. Property can be used in its entirety, or use what you need and market the permitted land parcels to others. Currently there are 6 buildings onsite to include: 1792 sq ft office building; 3364 sq ft garage building with heat, loading dock, and rail siding; 7544 sq ft open span, no ceilings, storage building; 3 additional storage buildings. Property includes an owned rail siding for direct shipment possibilities. Highway access is on Route 11 East, 3/10's of a mile from Route 103, and 9 miles to Route 91, exit 6. Office building has center entry and two administration wings, could be used by two or more businesses. Fiber-optic internet is on site. Garage building is currently used for service of trucking and excavation equipment and includes office area. This building has loading dock and direct access to rail siding. Large former ore shed with 7544 sq ft of open span. Multiple doors to access the building. Survey and permits in place for 7 lot subdivision of the industrial park. Common rail siding to be maintained for all. Currently there is a tenant in the office building. Also offered separately (building lot, ore shed building, or garage/office/storage buildings). Video attached to the MLS.

Listed by Betty McEnaney and Andy Paluch of TPW Real Estate

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 2.98% last updated on 2021-04-29

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

141 Stage Road Chester VT 05143

Chester, VT141 Stage Road

Price$999,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4822981

  • Land
  • Acreage 548
  • Area Near Skiing, Rural
  • Utilities None
  • Zoning Residential

Don't miss the rare opportunity to own this spectacular acreage set between the rolling hills outside the beautiful villages of Chester and Grafton Vermont. The stunning 543 +/- acres has it all. Made up of 5 contiguous preexisting lots the parcel has road frontage on Stage Road in Chester giving multiple opportunities for a number of small subdivisions. Three lots also front onto route 35 between Chester and Grafton which includes two 70 +/- acres lots as well as a 20.1 acre lot with permitted 1 acre +/- Mica Schist stone quarry. There are also gravel deposits on the site which could be used to develop the logging trails further. If you have conservation on your mind the entire lot is enrolled in the Vermont Value use program which helps to keep the taxes low. The interior of the lot is mostly wooded and hosts a large open area for staging a logging operation. There are also a network of marked logging trails throughout the property making it easily accessible. The beautifully crafted ponds throughout offer a welcome spot to take in the beauty of the landscape as well attracting all manner of wildlife. The seller will entertain selling individual lots separately. Whether you wish to develop or keep this pristine site as is you will find endless choices and opportunity for this very special place. Come see today!!

Listed by Daire Gibney of Barrett and Valley Associates, Inc/Chest

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 2.98% last updated on 2021-04-29

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

816 Popple Dungeon Road Chester VT 05143

Chester, VT816 Popple Dungeon Road

Price$979,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4848206

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 2,676

Welcome to Deer Valley Farm also known as the Williams Homestead. This is the first time the property has been offered for sale in over 60 years! The home has been lovingly cared for with lots of improvements over the decades of ownership. Outside: The barn has undergone major work which insures its stability for years to come and includes a wine cellar. It measures 45x105 with plenty of room for cars, toys or animals. Other improvements include stonework, tennis court and pool with pool house and gardens. The walking bridge over the Williams River includes 4 staircases to the river and built in lights. The home is styled with Italian tile throughout and offers cozy antique charm with 3 fireplaces. The home does need updating but will be well worth the effort. The structure itself has been well maintained. The large acreage easily lends itself to a few other incredible homesites. Located just outside the town of Chester less than 4 hours to NYC and 2.5 hours to Boston. Minutes to all of Southern Vermont amenities including Okemo, Stratton, Killington, Vermont Country Store, Weston Playhouse, world-class golf and the shops in Manchester. This property will not disappoint.

Listed by Lisa Kelley of Cummings & Co

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 2.98% last updated on 2021-04-29

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

321 Main Street Chester VT 05143

Chester, VT321 Main Street

Price$899,000The price has recently decreased

MLS Number 4811623

  • Commercial
  • Year Built 1854
  • Acreage 0.28

Inn Victoria offers a new owner the opportunity to step into a very successful operation business. The Inn has 9 guest bedrooms all with private baths, assistant managers suite of 10th bedroom, plus 1,000 sq ft owners quarters, first floor professional laundry facility and large public spaces which are beautifully decorated and well maintained. The outdoor patio and wedding garden with 3 large pergolas is idea for small gatherings. The annual occupancy and average daily rate is higher than most B&B's of this size. It is a testament to the current owners sincere dedication to the business and providing a wonderful guest experience. The Inn is a member of a 4 Inn to Inn walking group. The revenue from the Inn to Inn walking tours is substantial. It attracts guests from all over the world. The location is only a few miles from I-91, a north south interstate on the east side of Vermont allowing millions of people within a 4 hour drive to visit the INN. There is also upside to the revenue with an enhanced marketing plan. The Village of Chester is considered one of the most picturesque Villages in Vermont. You do not want to miss out on this opportunity if you are serious about owning a B&B. Benefits of Inn Victoria Written by the Sellers can be found under "D" below the picture above.

Listed by Dick Palmer of Hospitality Consultants, LLC

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 2.98% last updated on 2021-04-29

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

698 Vermont RT 11 Route Chester VT 05143

Chester, VT698 Vermont RT 11 Route

Price$699,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4820671

  • Residential Single Family
  • Construction Existing
  • Bedrooms 10
  • Bathroom 12
  • Square Feet 6,848

An Amazing opportunity to own a 1810 Brick federal style home that is rich in local history and one of the most historic homes in Chester. It's had many reincarnations over the 2 century's of its existence. Starting as an old farmhouse it was converted to an Inn in 1942 and has been run as one ever since. It's been known as the Stone Hearth Inn and Tavern since 1982. It has been beautifully cared for by its current owners who have updated and maintained its elegance and down home charm. The Inn features 8 bedrooms mostly en-suite, a large formal dining room, Formal living room with a classic stone fireplace, office and a commercial kitchen. The home also features a separate 700 sq ft apt for additional income possibilities. Upstairs is a 2 bedroom owners quarters with full bath and living room. Attached to the Inn/Home is the 80 seat Tavern with refinished wood floors, gorgeous wood bar and wood stove. The property is special. Nearly 6 acres of open space, perennial gardens, back patio and direct groomed access to the VAST snowmobile trails. The possibilities here are endless. Large family home to live and work with great income potential with rentals, restaurant, tavern and even weddings. Run it or lease the spaces out. Ski clubs are another great possibility. Located just 2 miles from the Chester Green and only a short distance to major ski resorts, Okemo, Stratton, Bromley and Magic. Live the Vermont dream at this fantastic property.

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 2.98% last updated on 2021-04-29

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

698 VT ROUTE 11 West Chester VT 05143

Chester, VT698 VT ROUTE 11 West

Price$699,000The price has recently decreased

MLS Number 4820670

  • Commercial
  • Year Built 1810
  • Acreage 5.63

An Amazing opportunity to own a 1810 Brick federal style home that is rich in local history and one of the most historic homes in Chester. It's had many reincarnations over the 2 century's of its existence. Starting as an old farmhouse it was converted to an Inn in 1942 and has been run as one ever since. It's been known as the Stone Hearth Inn and Tavern since 1982. It has been beautifully cared for by its current owners who have updated and maintained its elegance and down home charm. The Inn features 8 bedrooms mostly en-suite, a large formal dining room, Formal living room with a classic stone fireplace, office and a commercial kitchen. The home also features a separate 700 sq ft apt for additional income possibilities. Upstairs is a 2 bedroom owners quarters with full bath and living room. Attached to the Inn/Home is the 80 seat Tavern with refinished wood floors, gorgeous wood bar and wood stove. The property is special. Nearly 6 acres of open space, perennial gardens, back patio and direct groomed access to the VAST snowmobile trails. The possibilities here are endless. Large family home to live and work with great income potential with rentals, restaurant, tavern and even weddings. Run it or lease the spaces out. Ski clubs are another great possibility. Located just 2 miles from the Chester Green and only a short distance to major ski resorts, Okemo, Stratton, Bromley and Magic. Live the Vermont dream at this fantastic property.

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 2.98% last updated on 2021-04-29

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

2206 Green Mountain Turnpike Chester VT 05143

Chester, VT2206 Green Mountain Turnpike

Price$659,000The price has recently decreased

Active With Contract

MLS Number 4832640

  • Commercial
  • Year Built 1790
  • Acreage 35

Have you always dreamed of owning a charming Bed & Breakfast in a picturesque Vermont town? Now is your chance! Take advantage of a rare opportunity to purchase this busy Inn on the historic Green Mountain Turnpike (a peaceful country road) in beautiful Chester, Vermont. This grand late 1700's former stagecoach Inn and tavern, which sits on 35 acres of woods, meadow, and lawn, has retained the charm of an earlier time and offers many original features, including wide plank pine floors, Rumford fireplaces, hand-hewn beams, a beehive oven, authentic Moses Eaton stenciling (hidden near a secret third staircase), and Chester's first hot water bathtub. The Inn features nine bright and spacious guestrooms, all with their own private baths and great views, as well as a spacious owner's quarters, an Inn office and a lovely stone garage. Guests enjoy meals in the comfortable country dining room, relax on the back porch and in the guest parlor by the fireplace while mingling with fellow visitors. There is plenty of space for all to enjoy inside and out. Your guests and your family will love the beautiful natural surroundings in every season including a private, spring-fed pond and acres of meadow, woods and paths for hiking, swimming, ice skating, snowshoeing and cross-country skiing-right on the premises! The setting is quiet, serene, peaceful, and only minutes away from the Village of Chester + 5 major ski resorts. This property has not been offered for sale for over 20 years.

Listed by Hergenrother Realty Group and Terri Naroian of KW Vermont

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 2.98% last updated on 2021-04-29

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

2206 Green Mountain Turnpike Chester VT 05143

Chester, VT2206 Green Mountain Turnpike

Price$639,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4832641

  • Residential Single Family
  • Construction Existing
  • Bedrooms 12
  • Bathroom 12
  • Square Feet 6,976

Come fall in love with Vermont and this charming late 1700s colonial farmhouse set in a quintessential country location. With 35 acres to call your own, and only minutes away from beautiful Chester Village, you will discover the peace and tranquility this safe and private property has to offer. Cherish its history as a stagecoach inn and tavern back in the 1700's with reminders of those earlier days with original wide-plank pine floors, Rumford fireplaces, and hand-hewn beams. Many possibilities are yours - use the 9 pleasantly furnished guest rooms as a bed & breakfast, airbnb or ski house. Or, enjoy as a large family home with plenty of space for home offices (with high-speed fiber optic wifi throughout), remote schooling, sewing/crafting, or home gym/yoga space. The third-floor owners' quarters can be a great spot for teens, older children returning home or visiting friends and family. Bright and spacious inside; breathtaking natural surroundings in every season. So much to enjoy right on the premises with your own spring-fed pond, acres of meadow, woods and paths for hiking, swimming, ice-skating, snowshoeing and cross-country skiing! Fall in love with it all - this one-of-a-kind Vermont home - as you relax comfortably on the back porch swing! This is Vermont peace and serenity at its finest!

Listed by Hergenrother Realty Group and Terri Naroian of KW Vermont

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 2.98% last updated on 2021-04-29

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

92 Vt Rte 11 west Chester VT 05143

Chester, VT92 Vt Rte 11 west

Price$599,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4818070

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 4
  • Square Feet 7,610

Built and operated as a successful retail/eat-in bakery/cafe for 20 years, this fascinating structure on 3.5+/- level acres offers possibility for use as a full time residence with a home business, or, with further modification, a unique and spectacular full time home. The amazing cathedral like structure was built in 1997 on an old homestead and attached to the barn which dates back to 1850s. The entire interior is connected and finished as one seamless space. There is a 4-flu chimney which could be made into a beautiful stone fireplace. The open floor plan could be redesigned for living space. The possibilities are endless. 4 bathroom spaces are in place with two half baths to code for public use and two more bath areas with a walk-in tiled shower. A home business such as a dance studio, music space, or any form of retail business would work very well with flexible options as to where the business entrance would be. Walking distance to town, adjoins town rec area.

Listed by Geralyn Donohue of Engel & Volkers Okemo-Woodstock

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 2.98% last updated on 2021-04-29

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

92 VT Rte 11 West Chester VT 05143

Chester, VT92 VT Rte 11 West

Price$599,000The price has recently decreased

MLS Number 4817827

  • Commercial
  • Year Built 1997
  • Acreage 3.5

Exceptional commercial opportunity in Chester on 3.5 acres +/- with over 7,000+/- sf of amazing space. Soaring cathedral ceilings and exposed arched beams culminate in a 34 ft high glass pyramid that creates a sense of ethereal balance. The fantastic structure is influenced by the spiritual philosophy of Rudolf Steiner and the great cathedrals of Europe. Anthroposophic shapes and symbols tied to meditative practice are reinforced throughout including a coptic cross design around the massive 4 flu chimney serving the ovens and a large window referencing a Pisces symbol. The building has radiant heat in the main space and a back-up generator standing by. Two Handicap access public bathrooms w/skylights are conveniently located near the front entrance. There are two more bathrooms, including a tiled walk-in shower with laundry area and two enclosed spaces for offices and privacy. The attached 1850's barn was thoughtfully renovated with exposed beams, a multi level second floor, loading dock, double glass door entrance with and even a dumb waiter! The building has wonderful acoustics and an open floor plan that would lend itself to many venues e.g., restaurant with a cooking school, dance studio or pub eatery. Seating capacity for 51. There is a large garden area for farm to table cafe/restaurants and two level, spacious lawns for outdoor venues. Fabulous location within walking distance to village and town rec area. Traffic count 4015.

Listed by Geralyn Donohue of Engel & Volkers Okemo-Woodstock

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 2.98% last updated on 2021-04-29

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

266 Main Street Chester VT 05143

Chester, VT266 Main Street

Price$579,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4845016

  • Residential Single Family
  • Construction Existing
  • Bedrooms 9
  • Bathroom 9
  • Acreage 0.75

This 1780's stunning yet quaint home in the heart of Chester and Southern Vermont is truly the ideal location for a spectacular private residence or successful hospitality business. Owned and operated with love this building has provided a warm welcome to all who have visited and have become enchanted with Vermont through the years. The period home with newly renovated 2 bedroom separate living quarters comes mostly furnished leaving you space to add your personal touches. The main floor is easily accessible with first floor accommodations for those needing to avoid stairs. Gracious rooms and cozy common areas invite you to relax in a central location allowing easy access exploring the surrounding Chester village and with mountains, lakes and streams all within short drive you will not lack options for fun and relaxation. Come see this charmer; you may want to stay awhile!

Listed by Daire Gibney of Barrett and Valley Associates, Inc/Chest

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 2.98% last updated on 2021-04-29

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Broker Reciprocity

Copyright 2021 New England Real Estate Network, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this web site comes in part from the IDX Program of NEREN. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated May 5, 2021.

 

Birch, Maple, Stone, Light, 8.04 +/- Acres

Mad River Valley Building Lot $98,500 Details

267.4 +/- Acres, Farmhouse, Barn, Meadows & Views

Gorgeous Home, Huge Acreage $1,288,000 Details

 

43+/- Breathtaking Acres, Mad River Valley Heirloom

3 Buildable Lots or One Treasure $1,100,000 Details